US20220011488A1 - Compound, polymerizable composition, cured product, optical film, polarizing plate, and image display device - Google Patents

Compound, polymerizable composition, cured product, optical film, polarizing plate, and image display device Download PDF

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US20220011488A1
US20220011488A1 US17/486,125 US202117486125A US2022011488A1 US 20220011488 A1 US20220011488 A1 US 20220011488A1 US 202117486125 A US202117486125 A US 202117486125A US 2022011488 A1 US2022011488 A1 US 2022011488A1
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Aiko YAMAMOTO
Hiroshi Inada
Shunya Katoh
Toshikazu SUMI
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Fujifilm Corp
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    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
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    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/302—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and two or more oxygen atoms in the alcohol moiety
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/12—Esters of phenols or saturated alcohols
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    • C08F222/245—Esters containing sulfur the ester chains containing seven or more carbon atoms
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    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • C09K19/3833—Polymers with mesogenic groups in the side chain
    • C09K19/3838—Polyesters; Polyester derivatives
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    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid

Definitions

  • the present invention relates to a compound, a polymerizable composition, a cured product, an optical film, a polarizing plate, and an image display device.
  • Optical films such as an optical compensation sheet and a phase difference film are used in various image display devices in order to eliminate image coloration or expand a viewing angle.
  • a stretched birefringent film has been used as the optical film, but in recent years, it has been proposed to use an optical film having an optically anisotropic layer (phase difference layer) consisting of a liquid crystalline compound instead of the stretched birefringent film.
  • a polymerizable liquid crystal composition for forming a phase difference layer containing a first rod-shaped compound having a cyano group at one end and a (meth)acrylate at the other end, a second rod-shaped compound having (meth)acrylates at both ends, and a quaternary ammonium salt” is described ([claim 1 ]); and as the second rod-shaped compound, a compound represented by Formula (2) is described ([claim 3 ]).
  • the present inventors have conducted studies on the polymerizable composition described in JP2013-164520A, and have thus found that in a case where a ring structure is further introduced into a second rod-shaped compound in order to widen a temperature range exhibiting liquid crystallinity from the viewpoint of production characteristics and the like, the temperature range exhibiting the liquid crystallinity of the compound were wider, but the solubility of the compound was deteriorated and it was difficult to suppress the precipitation.
  • an object of the present invention is to provide a compound having a wide temperature range exhibiting liquid crystallinity and excellent precipitation suppression and solubility; and a polymerizable composition, a cured product, an optical film, a polarizing plate, and an image display device, each using the compound.
  • the present inventors have conducted intensive studies to accomplish the object, and as a result, they have found that in a case where a compound has a predetermined structure, the compound has a wide temperature range exhibiting liquid crystallinity and excellent precipitation suppression and solubility, thereby completing the present invention.
  • a 1 represents an aromatic ring which may have a substituent or an alicyclic ring which may have a substituent.
  • Cy represents a 1,4-cyclohexylene group which may have a substituent, and the two Cy's may be the same as or different from each other.
  • D 1 , D 2 , and D 3 each independently represent a single bond, or a divalent linking group consisting of —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, —NR 1 —, or a combination of two or more thereof, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • SP 1 and SP 2 each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group obtained by each independently substituting one or more of —CHs-'s constituting a linear or branched alkylene group having 1 to 12 carbon atoms with —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, or —NR 1 —, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • k represents an integer of 1 to 3. In a case where k is 2 or 3, a plurality of A 1 's and D 2 's which are present in the formula may be the same as or different from each other.
  • L 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 or L 2 represents a polymerizable group.
  • B 2 , B 3 , B 5 , B 6 , B 7 , and B 8 each independently represent a hydrogen atom or a substituent. It should be noted that in a case where at least one of B 2 , B 3 , B 6 , or B 7 represents a substituent, the substituent does not include a ring structure.
  • a 1 and A 2 each independently represent an aromatic ring which may have a substituent or an alicyclic ring which may have a substituent.
  • D 1 , D 2 , D 3 , and D 4 each independently represent a single bond, or a divalent linking group consisting of —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 —CR 2 —, —NR 1 —, or a combination of two or more thereof, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • SP 1 and SP 2 each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group obtained by each independently substituting one or more of —CH 2 -'s constituting a linear or branched alkylene group having 1 to 12 carbon atoms with —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, or —NR 1 —, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • m is 2 or 3
  • a 1 's and D 2 's which are present in the formula may be the same as or different from each other.
  • n is 2 or 3
  • a 2 's and D 4 's which are present in the formula may be the same as or different from each other.
  • L 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 or L 2 represents a polymerizable group.
  • B 12 , B 13 , B 15 , B 16 , B 17 , and B 18 each independently represent a hydrogen atom or a substituent. It should be noted that in a case where at least one of B 12 , B 13 , B 16 , or B 17 represents a substituent, the substituent does not include a ring structure, and in a case where at least one of B 12 or B 13 represents a substituent, the substituent does not include —CHO.
  • B 2 , B 3 , B 5 , B 6 , B 7 , or B 8 in Formula (1) represents a substituent.
  • B 2 , B 3 , B 6 , or B 7 in Formula (1) represents a hydrogen atom.
  • B 12 , B 13 , B 16 , or B 17 in Formula (2) represents a hydrogen atom.
  • B 5 , B 6 , B 7 , or B 8 in Formula (1) represents a hydrogen atom.
  • B 15 , B 16 , B 17 , or B 18 in Formula (2) represents a hydrogen atom.
  • B 2 , B 3 , B 5 , or B 8 in Formula (1) represents a hydrogen atom.
  • B 12 , B 13 , B 15 , or B 18 in Formula (2) represents a hydrogen atom.
  • B 2 , B 3 , B 5 , B 6 , B 7 , or B 8 in Formula (1) represents a substituent
  • the substituent represents an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, a halogen group, a cyano group, a nitro group, an alkylthiol group, an N-alkylcarbamate group, an aryl group, an aryloxy group, an arylcarbonyl group, an arylcarbonyloxy group, an arylamino group, an arylamide group, an arylthiol group, an N-arylcarbamate group, a cycloalkyl group, a cycloalkyloxy group, a cycloalkyloxy group,
  • B 12 , B 13 , B 15 , B 16 , B 17 , or B 18 in Formula (2) represents a substituent
  • the substituent represents an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, halogen, a cyano group, a nitro group, an alkylthiol group, an N-alkylcarbamate group, an aryl group, an aryloxy group, an arylcarbonyl group, an arylcarbonyloxy group, an arylamino group, an arylamide group, an arylthiol group, an N-arylcarbamate group, a cycloalkyl group, a cycloalkyloxy group, a cycloalkylcarbon
  • a polymerizable composition comprising the compound as described in any one of [1] to [20].
  • a polarizing plate comprising:
  • An image display device comprising the optical film as described in [25] or the polarizing plate as described in [26].
  • the present invention it is possible to provide a compound having a wide temperature range exhibiting liquid crystallinity and excellent precipitation suppression and solubility; and a polymerizable composition, a cured product, an optical film, a polarizing plate, and an image display device, each using the compound.
  • FIG. 1A is a schematic cross-sectional view showing an example of the optical film of the present invention.
  • FIG. 1B is a schematic cross-sectional view showing an example of the optical film of the present invention.
  • FIG. 1C is a schematic cross-sectional view showing an example of the optical film of the present invention.
  • a numerical value range expressed using “to” means a range that includes the preceding and succeeding numerical values of “to” as the lower limit value and the upper limit value, respectively.
  • the content of the component refers to a total content of the substances used in combination unless otherwise specified.
  • the compound of an embodiment of the present invention is a compound represented by Formula (1) (hereinafter also simply referred to as a “compound (1)”) or a compound represented by Formula (2) (hereinafter also simply referred to as a “compound (2)”) which is other than the compound represented by Formula (1).
  • the compound having a structure represented by Formula (1) or (2) is a compound having a wide temperature range exhibiting liquid crystallinity and excellent precipitation suppression and solubility, as mentioned above.
  • naphthalene skeleton having a side chain structure at the first and fourth positions in the center (core) of the molecule an interaction between the cores was enhanced and stacking properties between the molecules were improved, whereby the upper limit temperature exhibiting liquid crystallinity was increased and the temperature range was widened.
  • the solubility was improved and the precipitation was suppressed.
  • the compound (1) is a compound represented by Formula (1).
  • a 1 represents an aromatic ring which may have a substituent or an alicyclic ring which may have a substituent.
  • Cy represents a 1,4-cyclohexylene group which may have a substituent, and the two Cy's may be the same as or different from each other.
  • D 1 , D 2 , and D 3 each independently represent a single bond, or a divalent linking group consisting of —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, —NR 1 —, or a combination of two or more thereof, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • SP 1 and SP 2 each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group obtained by each independently substituting one or more of —CH 2 -'s constituting a linear or branched alkylene group having 1 to 12 carbon atoms with —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, or —NR 1 —, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • k represents an integer of 1 to 3. In a case where k is 2 or 3, a plurality of A 1 's and D 2 's which are present in the formula may be the same as or different from each other.
  • L 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 or L 2 represents a polymerizable group.
  • B 2 , B 3 , B 5 , B 6 , B 7 , and B 8 each independently represent a hydrogen atom or a substituent. It should be noted that in a case where at least one of B 2 , B 3 , B 6 , or B 7 represents a substituent, the substituent does not include a ring structure.
  • examples of the aromatic ring shown in one aspect of A 1 include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring; and aromatic heterocycles such as a furan ring, a thiophene ring, a pyrrole ring, an oxazole ring, an isoxazole ring, an oxadiazole ring, a thiazole ring, an isothiazole ring, a thiadiazole ring, an imidazole ring, a pyrazole ring, a triazole ring, a furazan ring, a tetrazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazole ring, a tetrazine ring,
  • examples of the alicyclic ring shown in one aspect of A 1 include cycloalkane rings such as a cyclohexane ring, a cyclopeptane ring, a cyclooctane ring, a cyclododecane ring, and a cyclodocosane ring.
  • the cyclohexane ring (for example, a 1,4-cyclohexylene group) is preferable.
  • examples of the substituent which may be contained in the aromatic ring or the alicyclic ring include an alkyl group, an alkoxy group, and a halogen atom.
  • an alkyl group having 1 to 18 carbon atoms for example, a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, and a cyclohexyl group) is more preferable, an alkyl group having 1 to 4 carbon atoms is still more preferable, and the methyl group or the ethyl group is particularly preferable.
  • an alkyl group having 1 to 8 carbon atoms for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,
  • an alkoxy group having 1 to 18 carbon atoms is preferable, an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group, an ethoxy group, an n-butoxy group, and a methoxyethoxy group) is more preferable, an alkoxy group having 1 to 4 carbon atoms is still more preferable, and the methoxy group or the ethoxy group is particularly preferable.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among these, the fluorine atom or the chlorine atom is preferable.
  • a 1 in Formula (1) is preferably the alicyclic ring, more preferably the cycloalkane ring, still more preferably the cyclohexane ring, and particularly preferably the 1,4-cyclohexylene group.
  • D 1 , D 2 , and D 3 each independently represent a single bond, or a divalent linking group consisting of —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, —NR 1 —, or a combination of two or more thereof, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • the substituent is preferably the single bond, —CO—, —COO—, —OCO—, —CO—NH—, or —NH—CO—, more preferably —COO—, and still more preferably —OCO—.
  • D 2 present between two A 1 's is the single bond.
  • Suitable examples of the linear or branched alkylene group having 1 to 12 carbon atoms shown in one aspect of SP 1 and SP 2 in Formula (1) include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group, and a heptylene group.
  • SP 1 and SP 2 may be a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group obtained by each independently substituting one or more of —CH 2 -'s constituting a linear or branched alkylene group having 1 to 12 carbon atoms with —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, or —NR 1 —, as described above, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • k represents an integer of 1 to 3, and is preferably 2 or 3, and more preferably 2. Further, in a case where k is 2 or 3, a plurality of A 1 's and D 2 's which are present in the formula may be the same as or different from each other.
  • examples of the monovalent organic group represented by each of L 1 and L 2 include an alkyl group, an aryl group, and a heteroaryl group.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear.
  • the number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 10.
  • the aryl group may be a monocycle or a polycycle, but is preferably the monocycle.
  • the number of carbon atoms of the aryl group is preferably 6 to 25, and more preferably 6 to 10.
  • the heteroaryl group may be a monocycle or a polycycle.
  • the number of heteroatoms constituting the heteroaryl group is preferably 1 to 3.
  • the heteroatoms constituting the heteroaryl group is preferably a nitrogen atom, a sulfur atom, or an oxygen atom.
  • the number of carbon atoms of the heteroaryl group is preferably 6 to 18, and more preferably 6 to 12.
  • the alkyl group, the aryl group, and the heteroaryl group may be unsubstituted or have a substituent. Examples of the substituent include the same ones as the substituents which may be contained in A 1 in Formula (1).
  • the polymerizable group represented by at least one of L 1 or L 2 is not particularly limited, but is preferably a polymerizable group which is radically polymerizable or cationically polymerizable.
  • a generally known radically polymerizable group can be used as the radically polymerizable group, and suitable examples thereof include an acryloyl group and a methacryloyl group.
  • the acryloyl group generally has a high polymerization rate, and from the viewpoint of improvement of productivity, the acryloyl group is preferable but the methacryloyl group can also be used in the same manner as the polymerizable group.
  • a generally known cationically polymerizable group can be used as the cationically polymerizable group, and specific examples thereof include an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiroorthoester group, and a vinyloxy group.
  • the alicyclic ether group or the vinyloxy group is suitable, and an epoxy group, an oxetanyl group, or the vinyloxy group is particularly preferable.
  • Particularly preferred examples of the polymerizable group include the following groups.
  • both of L 1 and L 2 in Formula (1) are preferably a polymerizable group, and more preferably an acryloyl group or a methacryloyl group.
  • B 2 , B 3 , B 5 , B 6 , B 7 , and B 8 each independently represent a hydrogen atom or a substituent. It should be noted that in a case where at least one of B 2 , B 3 , B 6 , or B 7 represents a substituent, the substituent does not include a ring structure.
  • At least one of B 2 , B 3 , B 5 , B 6 , B 7 , or B 8 in Formula (1) represents a substituent (hereinafter also simply referred to as a “substituent B”).
  • examples of the substituent B include an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group, an N-alkylcarbamate group, an aryl group, an aryloxy group, an arylcarbonyl group, an arylcarbonyloxy group, an arylamino group, an arylamide group, an arylthiol group, an N-arylcarbamate group, a cycloalkyl group, a cycloalkyloxy group, a cycloalkylcarbonyl group, a cycloalkylcarbonyloxy group, a cycloalkylamino group,
  • the substituent does not include a ring structure
  • examples of the substituent B include an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group, an N-alkylcarbamate group, and a monovalent organic group obtained by substituting one or more —CH 2 -'s constituting an alkyl group with —O— or —CO—.
  • the alkyl group, the alkoxy group, the alkoxycarbonyl group, or the alkylcarbonyloxy group is preferable.
  • an alkyl group having 1 to 18 carbon atoms for example, a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, and a cyclohexyl group) is more preferable, an alkyl group having 1 to 4 carbon atoms is still more preferable, and the methyl group or the ethyl group is particularly preferable.
  • an alkyl group having 1 to 8 carbon atoms for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,
  • an alkoxy group having 1 to 18 carbon atoms is preferable, an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group, an ethoxy group, an n-butoxy group, and a methoxyethoxy group) is more preferable, an alkoxy group having to 4 carbon atoms is still more preferable, and the methoxy group or the ethoxy group is particularly preferable.
  • alkoxycarbonyl group examples include a group in which an oxycarbonyl group (—O—CO— group) is bonded to the alkyl group exemplified above, and for example, the alkoxycarbonyl group is preferably a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, or an isopropoxycarbonyl group, and more preferably the methoxycarbonyl group.
  • alkylcarbonyloxy group examples include a group in which a carbonyloxy group (—CO—O— group) is bonded to the alkyl group exemplified above, and for example, the alkylcarbonyloxy group is preferably a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, or an isopropylcarbonyloxy group, and more preferably the methylcarbonyloxy group.
  • B 5 or B 8 in Formula (1) represents a substituent
  • B 2 , B 3 , B 6 , and B 7 in Formula (1) each represent a hydrogen atom
  • At least one of B 2 , B 3 , B 6 , or B 7 in Formula (1) represents a substituent.
  • B 2 or B 3 in Formula (1) represents a substituent
  • B 5 , B 6 , B 7 , and B 8 in Formula (1) each represent a hydrogen atom
  • B 6 or B 7 in Formula (1) represents a substituent
  • B 2 , B 3 , B 5 , and B 8 in Formula (1) each represent a hydrogen atom
  • the compound (1) include compounds (1-1) to compounds (1-17) represented by the following formulae. Moreover, since a group adjacent to the acryloyloxy group in the structure of the compound (1-14) represents a propylene group (a group obtained by substituting a methyl group with an ethylene group), the compound 1-14 represents a mixture of regioisomers in which the positions of the methyl groups are different.
  • the compound (2) is a compound obtained by removing the compound represented by Formula (1) from the compound represented by Formula (2).
  • the compound corresponding to Formula (1) is referred to as a compound (1)
  • the compound not corresponding to Formula (1) but corresponding to Formula (2) is referred to as a compound (2).
  • a 1 and A 2 each independently represent an aromatic ring which may have a substituent or an alicyclic ring which may have a substituent.
  • D 1 , D 2 , D 3 , and D 4 each independently represent a single bond, or a divalent linking group consisting of —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 —CR 2 —, —NR 1 —, or a combination of two or more thereof, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • SP 1 and SP 2 each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group obtained by each independently substituting one or more of —CH 2 -'s constituting a linear or branched alkylene group having 1 to 12 carbon atoms with —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, or —NR 1 —, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • a 1 's and D 2 's which are present in the formula may be the same as or different from each other.
  • n is 2 or 3
  • a 2 's and D 4 's which are present in the formula may be the same as or different from each other.
  • L 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 or L 2 represents a polymerizable group.
  • B 12 , B 13 , B 15 , B 16 , B 17 , and B 18 each independently represent a hydrogen atom or a substituent. It should be noted that in a case where at least one of B 12 , B 13 , B 16 , or B 17 represents a substituent, the substituent does not include a ring structure, and in a case where at least one of B 12 or B 13 represents a substituent, the substituent does not include —CHO.
  • a 1 and A 2 are the same as A 1 described in Formula (1). Further, suitable aspects of A 1 and A 2 in Formula (2) are preferably the same as the suitable aspects of A 1 in Formula (1), that is, an aromatic ring that is not limited to an alicyclic ring.
  • D 1 , D 2 , D 3 , and D 4 each represent a single bond, or a divalent linking group consisting of —O—, —CO—, —S—, —C( ⁇ S)—, —CR 1 R 2 —, —CR 1 ⁇ CR 2 —, —NR 1 —, or a combination of two or more thereof, and R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • the substituent is preferably the single bond, —CO—, —COO—, —OCO—, —CO—NH—, or —NH—CO—, more preferably —COO—, and still more preferably —OCO—.
  • D 2 present between a plurality of A 1 's is —COO— or —OCO—.
  • n 2 or 3
  • D 4 present between a plurality of A 2 's is —COO— or —OCO—.
  • SP 1 and SP 2 are the same as SP 1 and SP 2 described in Formula (1), respectively.
  • n and n are each independently preferably 2 or 3, and more preferably 2. Further, in a case where m is 2 or 3, A 1 's and D 2 's which are present in the formula may be the same as or different from each other. Similarly, in a case where n is 2 or 3, a plurality of A 2 's and D 4 's which are present in the formula may be the same as or different from each other.
  • L 1 and L 2 are the same as L 1 and L 2 described in Formula (1), respectively.
  • B 12 , B 13 , B 15 , B 16 , B 17 , and B 18 each independently represent a hydrogen atom or a substituent. It should be noted that in a case where at least one of B 12 , B 13 , B 16 , or B 17 represents a substituent, the substituent does not include a ring structure, and in a case where at least one of B 12 or B 13 represents a substituent, the substituent does not include —CHO.
  • At least one of B 12 , B 13 , B 15 , B 16 , B 17 , or B 18 in Formula (2) represents a substituent.
  • examples of the substituent include the same ones as the substituent B described for B 1 and the like in Formula (1).
  • the substituent does not include a ring structure
  • examples of the substituent B include an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group, an N-alkylcarbamate group, a sulfonic acid ester group, and a monovalent organic group obtained by substituting one or more —CH 2 -'s constituting an alkyl group with —O— or —CO—.
  • B 15 or B 18 in Formula (2) represents a substituent
  • B 12 , B 13 , B 16 , and B 17 in Formula (2) each represent a hydrogen atom
  • At least one of B 12 , B 13 , B 16 , or B 17 in Formula (2) represents a substituent.
  • B 12 or B 13 in Formula (2) represents a substituent
  • B 15 , B 16 , B 17 , and B 18 in Formula (2) each represent a hydrogen atom
  • B 16 or B 17 in Formula (2) represents a substituent
  • B 12 , B 13 , B 15 , and B 18 in Formula (2) each represent a hydrogen atom
  • the compound (2) include a compound (2-1) and a compound (2-2) represented by the following formulae.
  • the polymerizable composition of an embodiment of the present invention is a polymerizable composition containing the above-mentioned compound of the embodiment of the present invention.
  • the polymerizable composition of the embodiment of the present invention preferably contains a polymerizable liquid crystal compound different from the above-mentioned compound of the embodiment of the present invention.
  • the polymerizable liquid crystal compound means a liquid crystal compound having a polymerizable group.
  • the liquid crystal compounds can be generally classified into a rod-shaped type and a disk-shaped type according to the shape thereof. Each of the types can further be classified into a low-molecular-weight type and a high-molecular-weight type.
  • the expression, being high-molecular generally refers to having a degree of polymerization of 100 or more (Polymer Physics-Phase Transition Dynamics, by Masao Doi, page 2, published by Iwanami Shoten, Publishers, 1992).
  • any of liquid crystal compounds can be used, but a rod-shaped liquid crystalline compound or a discotic liquid crystalline compound (disk-shaped liquid crystalline compound) is more preferably used.
  • the polymerizable liquid crystal compound preferably has two or more polymerizable groups in one molecule from the viewpoint of immobilization of the above-mentioned liquid crystal compound.
  • the type of the polymerizable group is not particularly limited, a functional group capable of performing an addition polymerization reaction is preferable, and an ethylenically unsaturated polymerizable group or a polymerizable ring group is more preferable. More specifically, preferred examples of the polymerizable group include an acryloyl group, a methacryloyl group, a vinyl group, a styryl group, and an allyl group, and the acryloyl group or the methacryloyl group is more preferable.
  • the rod-shaped liquid crystalline compound for example, the rod-shaped liquid crystalline compounds described in claim 1 of JP1999-513019A (JP-H11-513019A) or paragraphs [0026] to [0098] of JP2005-289980A can be preferably used, and as the discotic liquid crystal compound, for example, the discotic liquid crystalline compounds described in paragraphs [0020] to [0067] of JP2007-108732A and paragraphs [0013] to [0108] of JP2010-244038A can be preferably used, but the rod-shaped liquid crystalline compound is not limited thereto.
  • a reverse wavelength dispersible liquid crystal compound can be used as the polymerizable liquid crystal compound.
  • the “reverse wavelength dispersible” liquid crystal compound means that in a case where an in-plane retardation (Re) value at a specific wavelength (visible light range) of a phase difference film manufactured using the polymerizable liquid crystal compound is measured, the Re value is equal or higher as a measurement wavelength is increased.
  • Re in-plane retardation
  • the reverse wavelength dispersible liquid crystal compound is not particularly limited as long as it can form the reverse wavelength dispersible film as described above, and for example, the compound represented by General Formula (I) described in JP2008-297210A (in particular, the compounds described in paragraph Nos. [0034] to [0039]), the compounds represented by General Formula (I) described in JP2010-084032A (in particular, the compounds described in paragraph Nos. [0067] to [0073]), the compound represented by General Formula (II) described in JP2016-053709A (in particular, the compounds described in paragraph Nos. [0036] to [0043]), the compounds represented by General Formula (1) described in JP2016-081035A (in particular, the compounds described in paragraph Nos. [0043] to [0055]), or the like can be used.
  • the compound represented by General Formula (I) described in JP2008-297210A in particular, the compounds described in paragraph Nos. [0034] to [0039]
  • suitable examples of the polymerizable liquid crystal compound include compounds represented by Formulae (1) to (10), and specifically include the compounds having side chain structures shown in Table 1 and 2 below as K (side chain structure) in Formulae (1) to (10).
  • a group adjacent to each of the acryloyloxy group and the methacryloyl group represents a propylene group (a group in which a methyl group is substituted with an ethylene group), and represents a mixture of regioisomers in which the positions of the methyl groups are different.
  • the polymerizable composition of the embodiment of the present invention preferably contains a polymerization initiator.
  • the polymerization initiator to be used is preferably a photopolymerization initiator capable of initiating a polymerization reaction upon irradiation with ultraviolet rays.
  • photopolymerization initiator examples include ⁇ -carbonyl compounds (described in each of the specifications of U.S. Pat. Nos. 2,367,661A and 2,367,670A), acyloin ethers (described in the specification of U.S. Pat. No. 2,448,828A), ⁇ -hydrocarbon-substituted aromatic acyloin compounds (described in the specification of U.S. Pat. No. 2,722,512A), multinuclear quinone compounds (described in each of the specifications of U.S. Pat. Nos.
  • JP1988-40799B JP-S63-40799B
  • JP1993-29234B JP-H05-29234B
  • JP1998-95788A JP-H10-95788A
  • JP1998-29997A JP-H10-29997A
  • the polymerization initiator is an oxime-type polymerization initiator, and specific examples of the polymerization initiator include the initiators described in paragraphs [0049] to [0052] of WO2017/170443A.
  • the polymerizable composition of the embodiment of the present invention contains a solvent from the viewpoint of workability for forming a cured product (for example, an optically anisotropic layer) of an embodiment of the present invention, which will be described later.
  • the solvent include ketones (for example, acetone, 2-butanone, methyl isobutyl ketone, cyclohexanone, and cyclopentanone), ethers (for example, dioxane and tetrahydrofuran), aliphatic hydrocarbons (for example, hexane), alicyclic hydrocarbons (for example, cyclohexane), aromatic hydrocarbons (for example, toluene, xylene, and trimethylbenzene), halogenated carbons (for example, dichloromethane, dichloroethane, dichlorobenzene, and chlorotoluene), esters (for example, methyl acetate, ethyl acetate, and butyl acetate), water, alcohols (for example, ethanol, isopropanol, butanol, and cyclohexanol), cellosolves (for example, methyl cellosolve and ethyl cell
  • the polymerizable composition of the embodiment of the present invention contains a leveling agent from the viewpoint that the surface of a cured product of an embodiment of the present invention, which will be described later, is maintained smooth and the alignment is easily controlled.
  • Such a leveling agent is preferably a fluorine-based leveling agent or a silicon-based leveling agent for a reason that it has a high leveling effect on the addition amount, and the leveling agent is more preferably a fluorine-based leveling agent from the viewpoint that it is less likely to cause bleeding (bloom or bleed).
  • the leveling agent include the compounds described in paragraphs [0079] to [0102] of JP2007-069471A, the compound represented by General Formula (I) described in JP2013-047204A (in particular, the compounds described in paragraphs [0020] to [0032]), the compound represented by General Formula (1) described in JP2012-211306A (in particular, the compounds described in paragraphs [0022] to [0029]), the liquid crystal alignment accelerator represented by General Formula (1) described in JP2002-129162A (in particular, the compounds described in paragraphs [0076] to [0078] and [0082] to [0084]), and the compounds represented by General Formulae (I), (II), and (III) described in JP2005-099248A (in particular, the compounds described in paragraphs [0092] to [0096]).
  • the leveling agent may also function as an alignment control agent which will be described later.
  • the polymerizable composition of the embodiment of the present invention can contain an alignment control agent, as desired.
  • various alignment states such as homeotropic alignment (vertical alignment), tilt alignment, hybrid alignment, and cholesteric alignment can be formed, in addition to the homogeneous alignment, and specific alignment states can be controlled and achieved more uniformly and more accurately.
  • an alignment control agent which accelerates the homogeneous alignment for example, a low-molecular-weight alignment control agent or a high-molecular-weight alignment control agent can be used.
  • examples of the alignment control agent that forms or accelerates the homeotropic alignment include a boronic acid compound and an onium salt compound, and specifically, reference can be made to the compounds described in paragraphs [0023] to [0032] of JP2008-225281A, paragraphs [0052] to [0058] of JP2012-208397A, paragraphs [0024] to [0055] of JP2008-026730A, paragraphs [0043] to [0055] of JP2016-193869A, and the like, the contents of which are hereby incorporated by reference.
  • the cholesteric alignment can be achieved by adding a chiral agent to the composition of the embodiment of the present invention, and it is possible to control the direction of revolution of the cholesteric alignment by its chiral direction.
  • a content thereof is preferably 0.01% to 10% by mass, and more preferably 0.05% to 5% by mass with respect to the mass of the total solid content of the composition. In a case where the content is within the range, it is possible to obtain a cured product which has no precipitation or phase separation, alignment defects, or the like, and is uniform and highly transparent while achieving a desired alignment state.
  • These alignment control agents can further impart a polymerizable functional group, in particular, a polymerizable functional group that is polymerizable with the compound (I) included in the composition of the embodiment of the present invention.
  • the polymerizable composition of the embodiment of the present invention may contain components other than the above-mentioned components, and examples of such other components include a surfactant, a tilt angle control agent, an alignment assistant, a plasticizer, and a crosslinking agent.
  • the cured product of the embodiment of the present invention is a cured product obtained by curing the above-mentioned polymerizable composition of the embodiment of the present invention.
  • the polymerizable composition of the embodiment of the present invention contains, for example, a polymerizable liquid crystal compound different from the above-mentioned compound (I) together with the compound (I), it is possible to form an optically anisotropic layer as a cured product by polymerizing the polymerizable composition of the embodiment of the present invention.
  • Examples of a method for forming the cured product include a method in which the above-mentioned polymerizable composition of the embodiment of the present invention is used to cause a desired alignment state, and then fixed by polymerization.
  • the polymerization conditions are not particularly limited, but in the polymerization by irradiation with light, ultraviolet rays are preferably used.
  • the irradiation dose is preferably 10 mi/cm 2 to 50 J/cm 2 , more preferably 20 mJ/cm 2 to 5 J/cm 2 , still more preferably 30 mJ/cm 2 to 3 J/cm 2 , and particularly preferably 50 mJ/cm 2 to 1,000 mJ/cm 2 .
  • the polymerization may be carried out under a heating condition in order to accelerate the polymerization reaction.
  • the cured product can be formed on any of supports in the optical film of the embodiment of the present invention, which will be described later or a polarizer in the polarizing plate of an embodiment of the present invention, which will be described later.
  • the cured product of the embodiment of the present invention is preferably an optically anisotropic layer satisfying Formula (I).
  • Re(450) represents an in-plane retardation at a wavelength of 450 nm of the optically anisotropic layer
  • Re(550) represents an in-plane retardation at a wavelength of 550 nm of the optically anisotropic layer.
  • the measurement wavelength is 550 nm.
  • the values of the in-plane retardation and the thickness-direction retardation refer to values measured with light at the measurement wavelength using AxoScan OPMF-1 (manufactured by Opto Science, Inc.).
  • Rth ( ⁇ ) (( nx+ny )/2 ⁇ nz ) ⁇ d.
  • R0( ⁇ ) is expressed in a numerical value calculated with AxoScan OPMF-1, but means Re( ⁇ ).
  • such an optically anisotropic layer is preferably a positive A-plate or a positive C-plate, and more preferably the positive A-plate.
  • the positive A-plate (A-plate which is positive) and the positive C-plate (C-plate which is positive) are defined as follows.
  • nx a refractive index in a film in-plane slow axis direction (in a direction in which an in-plane refractive index is a maximum)
  • ny a refractive index in an in-plane direction orthogonal to the in-plane slow axis
  • nz a refractive index in a thickness direction
  • the positive A-plate satisfies the relationship of Formula (A1)
  • the positive C-plate satisfies the relationship of Formula (C1).
  • the positive A-plate has an Rth showing a positive value
  • the positive C-plate has an Rth showing a negative value.
  • the symbol, “ ⁇ ”, encompasses not only a case where the both are completely the same as each other but also a case where the both are substantially the same as each other.
  • nx ⁇ ny a case where (nx ⁇ ny) ⁇ d (in which d is the thickness of a film) is 0 to 10 nm, and preferably 0 to 5 nm is also included in “nx ⁇ ny”.
  • the Re(550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, still more preferably 130 to 150 nm, and particularly preferably 130 to 140 nm, from the viewpoint that the optically anisotropic layer functions as a ⁇ /4 plate.
  • the “ ⁇ /4 plate” is a plate having a ⁇ /4 function, specifically, a plate having a function of converting a linearly polarized light at a certain specific wavelength into a circularly polarized light (or converting a circularly polarized light to a linearly polarized light).
  • the optical film of the embodiment of the present invention is an optical film having the cured product of the embodiment of the present invention.
  • FIG. 1A , FIG. 1B , and FIG. 1C are each a schematic cross-sectional view showing an example of the optical film of the embodiment of the present invention.
  • FIG. 1 is a schematic view, and the thicknesses relationship, the positional relationship, and the like among the respective layers are not necessarily consistent with actual ones, and any of the support, the alignment film, and the hard coat layer shown in FIG. 1 are optional constitutional members.
  • An optical film 10 shown in FIG. 1 has a support 16 , an alignment film 14 , and an optically anisotropic layer 12 as the cured product in this order.
  • the optical film 10 may have a hard coat layer 18 on the side of the support 16 opposite to the side on which the alignment film 14 is provided as shown in FIG. 1B , and may have the hard coat layer 18 on the side of the optically anisotropic layer 12 opposite to the side on which the alignment film 14 is provided as shown in FIG. 1C .
  • the cured product contained in the optical film of the embodiment of the present invention is the above-mentioned cured product of the embodiment of the present invention.
  • the thickness of the cured product is not particularly limited, but in a case where the optical film functions as an optically anisotropic layer, the thickness of the cured product is preferably 0.1 to 10 ⁇ m, and more preferably 0.5 to 5 ⁇ m.
  • the optical film of the embodiment of the present invention may have a support as a base material for forming a cured product as described above.
  • Such a support is preferably transparent, and specifically, it preferably has a light transmittance of 80% or more.
  • Examples of such a support include a glass substrate and a polymer film, and examples of the material for the polymer film include cellulose-based polymers; acrylic polymers having an acrylic ester polymer such as polymethyl methacrylate and a lactone ring-containing polymer, thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene-based polymers such as polystyrene and an acrylonitrile-styrene copolymer (AS resin); polyolefin-based polymers such as polyethylene, polypropylene, and an ethylene-propylene copolymer; vinyl chloride-based polymers; amide-based polymers such as nylon and aromatic polyamide; imide-based polymers; sulfone-based polymers; polyether sulfone-based polymers; polyether ether ketone-based polymers; polyphenylene sulfide-based poly
  • the thickness of the support is not particularly limited, but is preferably 5 to 60 ⁇ m, and more preferably 5 to 30 ⁇ m.
  • the optical film of the embodiment of the present invention has any of the above-mentioned supports, it is preferable that the optical film has an alignment film between the support and the cured product. Further, an aspect in which the above-mentioned support may also function as an alignment film is also available.
  • the alignment film generally has a polymer as a main component.
  • Polymer materials for an alignment film are described in many documents, and many commercially available products can be used.
  • the polymer material used in the present invention is preferably a polyvinyl alcohol or a polyimide, or a derivative thereof. Particularly, a modified or non-modified polyvinyl alcohol is preferable.
  • Examples of the alignment film that can be used in the present invention include the alignment films described for Line 24 on Page 43 to Line 8 on Page 49 of WO01/88574A; the modified polyvinyl alcohols described in paragraphs [0071] to [0095] of JP3907735B; and the liquid crystal alignment film formed by a liquid crystal alignment agent described in JP2012-155308A.
  • a photo-alignment film is also preferably used as the alignment film.
  • the photo-alignment film is not particularly limited, but the polymer materials such as a polyamide compound and a polyimide compound, described in paragraphs 0024 to 0043 of WO2005/096041A; the liquid crystal alignment film formed by a liquid crystal alignment agent having a photo-alignment group, described in JP2012-155308A; LPP-JP265CP, trade name, manufactured by Rolic Technologies Ltd.; or the like can be used.
  • the thickness of the alignment film is not particularly limited, but from the viewpoint of forming an optically anisotropic layer having a uniform film thickness by alleviating the surface roughness that can be present on the support, the thickness is preferably 0.01 to 10 ⁇ m, more preferably 0.01 to 1 ⁇ m, and still more preferably 0.01 to 0.5 ⁇ m.
  • the optical film of the embodiment of the present invention has a hard coat layer in order to impart physical strength to the film.
  • the optical film may have the hard coat layer on the side of the support opposite to the side on which the alignment film is provided (see FIG. 1B ) or the optical film may have the hard coat layer on the side of the optically anisotropic layer opposite to the side on which the alignment film is provided (see FIG. 1C ).
  • the optical film of the embodiment of the present invention preferably includes an ultraviolet (UV) absorber, taking an effect of external light (particularly ultraviolet rays) into consideration.
  • UV ultraviolet
  • the ultraviolet absorber may be contained in the cured product of the embodiment of the present invention or may also be contained in a member other than the cured product constituting the optical film of the embodiment of the present invention. Suitable examples of the member other than the cured product include a support.
  • a benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorber is preferably used from the viewpoint that it has high ultraviolet absorptivity and ultraviolet absorbing ability (ultraviolet-shielding ability) used for an image display device is obtained.
  • two or more of ultraviolet absorbers having different maximum absorption wavelengths can be used in combination.
  • ultraviolet absorber examples include the compounds described in paragraphs [0258] and [0259] of JP2012-18395A and the compounds described in paragraphs [0055] to [0105] of JP2007-72163A.
  • Tinuvin 400 Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, and Tinuvin 1577 (all manufactured by BASF), or the like can be used.
  • a polarizing plate of an embodiment of the present invention has the above-mentioned optical film of the embodiment of the present invention and a polarizer. Furthermore, in a case where the optically anisotropic layer as the above-mentioned cured product of the embodiment of the present invention is a ⁇ /4 plate (positive A-plate), the polarizing plate of the embodiment of the present invention can be used as a circularly polarizing plate.
  • an angle between the slow axis of the ⁇ /4 plate and the absorption axis of a polarizer which will be described later is preferably 30° to 60°, more preferably 40° to 50°, still more preferably 42° to 48°, and particularly preferably 45° in the polarizing plate of the embodiment of the present invention.
  • the “slow axis” of the ⁇ /4 plate means a direction in which the refractive index in the plane of the ⁇ /4 plate is a maximum
  • the “absorption axis” of the polarizer means a direction in which the absorbance is highest.
  • a polarizer contained in a polarizing plate of an embodiment of the present invention is not particularly limited as long as it is a member having a function of converting light into specific linearly polarized light, and an absorptive type polarizer and a reflective type polarizer, which are known in the related art, can be used.
  • An iodine-based polarizer, a dye-based polarizer using a dichroic dye, a polyene-based polarizer, or the like is used as the absorptive type polarizer.
  • the iodine-based polarizer and the dye-based polarizer are classified into a coating type polarizer and a stretching type polarizer, any of which can be applied, but a polarizer which is manufactured by allowing polyvinyl alcohol to adsorb iodine or a dichroic dye and performing stretching is preferable.
  • examples of a method of obtaining a polarizer by carrying out stretching and dyeing in a state of a laminated film in which a polyvinyl alcohol layer is formed on a base material include the methods disclosed in JP5048120B, JP5143918B, JP4691205B, JP4751481B, and JP4751486B, and known technologies relating to these polarizers can also be preferably used.
  • a polarizer in which thin films having different birefringence are laminated, a wire grid-type polarizer, a polarizer having a combination of a cholesteric liquid crystal having a selective reflection range and a 1 ⁇ 4 wavelength plate, or the like is used as the reflective type polarizer.
  • a polymer containing a polyvinyl alcohol-based resin (—CH 2 —CHOH— as a repeating unit) since of its superior adhesion.
  • a polarizer containing at least one selected from the group consisting of polyvinyl alcohol and an ethylene-vinyl alcohol copolymer is preferable.
  • the thickness of the polarizer is not particularly limited, but is preferably 3 ⁇ m to 60 ⁇ m, more preferably 5 ⁇ m to 30 ⁇ m, and still more preferably 5 ⁇ m to 15 ⁇ m.
  • the polarizing plate of the embodiment of the present invention may have a pressure sensitive adhesive layer arranged between the cured product in the optical film of the embodiment of the present invention and the polarizer.
  • Examples of the pressure sensitive adhesive that can be used in the present invention include a polyvinyl alcohol-based pressure sensitive adhesive, but the pressure sensitive adhesive is not limited thereto.
  • An image display device of an embodiment of the present invention is an image display device having the optical film of the embodiment of the present invention or the polarizing plate of the embodiment of the present invention.
  • a display element used in the image display device of the embodiment of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescent (hereinafter simply referred to as “EL”) display panel, and a plasma display panel.
  • EL organic electroluminescent
  • the liquid crystal cell and the organic EL display panel are preferable, and the liquid crystal cell is more preferable. That is, as the image display device of the embodiment of the present invention, a liquid crystal display device using a liquid crystal cell as a display element or an organic EL display device using an organic EL display panel as a display element is preferable, and the liquid crystal display device is more preferable.
  • a liquid crystal display device which is an example of the image display device of the embodiment of the present invention is a liquid crystal display device having the above-mentioned polarizing plate of the embodiment of the present invention and a liquid crystal cell.
  • the polarizing plate of the embodiment of the present invention is used as the polarizing plate of the front side, and it is more preferable that the polarizing plate of the embodiment of the present invention is used as the polarizing plates on the front and rear sides, among the polarizing plates provided on the both sides of the liquid crystal cell.
  • liquid crystal cell constituting the liquid crystal display device will be described in detail.
  • the liquid crystal cell used for the liquid crystal display device is preferably in a vertical alignment (VA) mode, an optically compensated bend (OCB) mode, an in-plane-switching (IPS) mode, or a twisted nematic (TN) mode, but is not limited thereto.
  • VA vertical alignment
  • OBC optically compensated bend
  • IPS in-plane-switching
  • TN twisted nematic
  • rod-shaped liquid crystal molecules are substantially horizontally aligned and are twist-aligned at 60° to 120° during no voltage application thereto.
  • a TN-mode liquid crystal cell is most often used in a color TFT liquid crystal display device and described in numerous documents.
  • a VA-mode liquid crystal cell rod-shaped liquid crystal molecules are substantially vertically aligned during no voltage application thereto.
  • the VA-mode liquid crystal cell include (1) a VA-mode liquid crystal cell in the narrow sense of the word, in which rod-shaped liquid crystal molecules are substantially vertically aligned during no voltage application thereto, but are substantially horizontally aligned during voltage application thereto (described in JP1990-176625A (JP-H02-176625A)), (2) an MVA-mode liquid crystal cell in which the VA mode is multi-domained for viewing angle enlargement (described in SID97, Digest of Tech.
  • liquid crystal cell in a mode (n-ASM mode) in which rod-shaped liquid crystal molecules are substantially vertically aligned during no voltage application thereto and are multi-domain-aligned during voltage application thereto (described in Seminar of Liquid Crystals of Japan, Papers (preprint), 58-59 (1998)), and (4) a survival-mode liquid crystal cell (announced in LCD International 98).
  • the liquid crystal cell may be of any of a patterned vertical alignment (PVA) type, an optical alignment type, and polymer-sustained alignment (PSA) type. Details of these modes are specifically described in JP2006-215326A and JP2008-538819A.
  • IPS-mode liquid crystal cell In an IPS-mode liquid crystal cell, rod-shaped liquid crystal molecules are aligned substantially parallel with respect to a substrate, and application of an electric field parallel to the substrate surface causes the liquid crystal molecules to respond planarly.
  • the IPS mode displays black in a state where no electric field is applied and a pair of upper and lower polarizing plates have absorption axes which are orthogonal to each other.
  • JP1998-54982A JP-H10-54982A
  • JP1999-202323A JP-H11-202323A
  • JP1997-292522A JP-H09-292522A
  • JP1999-133408A JP-H11-133408A
  • JP1999-305217A JP-H11-305217A
  • JP1998-307291A JP-H10-307291A
  • Suitable examples of the organic EL display device which is an example of the image display device of the embodiment of the present invention include an aspect which includes, from the visible side, a polarizer, a ⁇ /4 plate (a positive A-plate) including the optically anisotropic layer of the embodiment of the present invention, and an organic EL display panel in this order.
  • the organic EL display panel is a display panel composed of an organic EL device in which an organic light emitting layer (organic electroluminescent layer) is sandwiched between electrodes (between a cathode and an anode).
  • the configuration of the organic EL display panel is not particularly limited but a known configuration is adopted.
  • dimethyl 4,4′-dicyclohexane dicarboxylate 130 g
  • 86.3 g of potassium hydroxide pellets 86.3 g
  • 1,300 mL of cumene 1,300 mL of cumene
  • 10 mL of polyethylene glycol (PEG2000) 10 mL
  • the outside equipment was set to a temperature of 180° C., and heating and refluxing were continued for 20 hours while evaporating the solvent.
  • the progress of the reaction was confirmed by nuclear magnetic resonance (NMR), and after the completion of the reaction, the reaction solution was cooled, 1,300 mL of ethanol was added thereto, and the precipitated potassium salt was collected by filtration.
  • NMR nuclear magnetic resonance
  • this potassium salt was dissolved in 1,300 ml of water, concentrated hydrochloric acid was added thereto under ice-cooling until the pH of the system reached 3, and the precipitated carboxylic acid was collected by filtration to recover a crude product.
  • a compound (S-2-d) was synthesized by performing the reaction in the same manner as for the compound (S-1-d), except that 4-methylsulfonyloxybutyl acrylate was changed to 4-methylsulfonyloxybutyl methacrylate.
  • a compound (S-3-d) was synthesized by performing the reaction in the same manner as for the compound (S-1-d), except that 4-methylsulfonyloxybutyl acrylate was changed to 4-methylsulfonyloxyethyl acrylate.
  • a compound (S-4-d) was synthesized by performing the reaction in the same manner as for the compound (S-1-d), except that 4-methylsulfonyloxybutyl acrylate was changed to the compound (S-4-d1).
  • a compound (S-5-d) was synthesized by performing the reaction in the same manner as for the compound (S-1-d), except that 4-methylsulfonyloxybutyl acrylate was changed to the compound (S-5-d1).
  • a comparative compound 1 represented by the following formula was synthesized according to the description in JP2013-164520A.
  • phase transition temperature For each of the compounds synthesized in Examples and Comparative Examples, the phase transition temperature, the precipitation suppression, and the solubility were evaluated by methods shown below.
  • Two polarizers of an optical microscope (ECLIPSE E600 POL, manufactured by Nikon Corporation) were arranged so that they were orthogonal to each other, and a sample stand was set between the two polarizers.
  • the temperature was elevated up to an isotropic phase and then lowered at 5° C./min, and a temperature at which crystals were precipitated was recorded.
  • Example 1 “Compound 1-1) in Table 3 below, “230 or more” in the notation “Cr 185 SA 220 N 230 or more Is” means that “a polymerization proceeds at 230° C. or higher, and thus, a temperature during a phase transition to an isotropic phase cannot be measured”.
  • Cyclopentanone was added to 25 mg of each synthesized compound so that the concentration of each compound was 40% by mass, and the mixture was heated and stirred at 50° C. for 1 minute.
  • the mixture was left to stand at 20° C. for 10 minutes, and in a case where there is no undissolved residue or precipitation, it is determined that the mixture can be dissolved at 40% by mass.
  • cyclopentanone was further added to the mixture to reduce the concentration by 5% by mass, an operation of heating and stirring at 50° C. for 1 minute and then leaving the mixture stand at 20° C. for 10 minutes was repeatedly performed until there was no undissolved residue or precipitation, thereby confirming the solubility.
  • concentration values indicating the solubility are shown in Table 3. Further, in Table 3 below, “>40” indicates that the substance is dissolved at a concentration of 40% by mass, so that it can also be dissolved even at a concentration of 40% by mass or more, and “ ⁇ 5” indicates that the substance is dissolved at 5% by mass, and the undissolved residues and precipitation are observed.
  • Example 1 1-1 Cr 185 SA 220 N 230 or more Is recrystal D 20 174
  • Example 3 1-3 Cr 135-140 N 247 Is recrystal 115 C 20
  • Example 4 1-4 Cr 84 N 208 Is recrystal 50 B >40
  • Example 5 1-5 Cr 105 N 230
  • Example 6 1-6 Cr 117 SA 162 N 255 Is recrystal 110 C 35
  • Example 7 1-7 Cr 126 SA 201 Iso 250 or more Is C 25
  • Example 9 1-9 Cr 79 SA 155 N 228 Is recrystal 49 A 20
  • Example 10 1-10 Cr 110 SA 166.5 N 219 Is recrystal 70 B 30
  • a predetermined compound having a naphthalene skeleton having a side chain structure at the 1,4 position in the center (core) of the molecule serves as a compound having a wide temperature range exhibiting liquid crystallinity and excellent precipitation suppression and solubility (Examples 1 to 21).
  • the following coating liquid for forming an alignment film P-3 was applied onto a glass substrate using a #18 bar coater, and the glass substrate was dried with hot air at 100° C. for 120 seconds and then subjected to a rubbing treatment to form an alignment film P-3.
  • the following polymerizable composition was applied onto the alignment film P-3 by a spin coating method.
  • a polymerizable composition was applied onto the alignment film P-3 by a spin coating method by the same method as in Example 22, except that the compound (1-3) was not blended.
  • phase transition temperature of the polymerizable composition applied on the alignment film P-3 in Examples 22 to 30 and Comparative Example 3 was measured by a method shown below.
  • Two polarizers of an optical microscope (ECLIPSE E600 POL, manufactured by Nikon Corporation) were arranged so that they were orthogonal to each other, and a sample stand was set between the two polarizers.
  • a small amount of the prepared polymerizable composition was placed on a slide glass, and the slide glass was set on a hot stage placed on a sample stand. While observing the state of the sample with a microscope, a temperature range of the smectic phase (Sm) was calculated by measuring the upper limit temperature and the crystallization temperature of the smectic phase (Sm) while elevating the temperature to a nematic phase and then lowering the temperature at 10° C./min. The results are shown in Table 4 below.
  • the following composition was put into a mixing tank and stirred to dissolve the respective components to prepare a cellulose acetate solution for use as a core layer cellulose acylate dope.
  • Core layer cellulose acylate dope Cellulose acetate having a degree of acetyl substitution of 2.88 100 parts by mass Polyester compound B described in Examples of JP2015-227955A 12 parts by mass
  • Matting agent solution Silica particles with an average particle size of 20 nm 2 parts by mass (AEROSIL R972, manufactured by Nippon Aerosil Co., Ltd.) Methylene chloride (first solvent) 76 parts by mass Methanol (second solvent) 11 parts by mass The core layer cellulose aeylate dope 1 part by mass
  • the core layer cellulose acylate dope and the outer layer cellulose acylate dope were filtered through a filter paper having an average pore diameter of 34 ⁇ m and a sintered metal filter having an average pore diameter of 10 ⁇ m, and then all the three layers of the core layer cellulose acylate dope and the outer layer cellulose acylate dopes arranged on both sides thereof were simultaneously cast on a metal band at 20° C. from a casting port (band caster).
  • the formed film was peeled from the metal band in a state where the solvent content was approximately 20% by mass, and the both ends of the film in the width direction were fixed with a tenter clip and dried while stretching the film at a stretch ratio of 1.1 times in the transverse direction. Thereafter, by transporting the film between rolls of a heat treatment device, the film was further dried and rolled to manufacture a long cellulose acylate film 1 having a thickness of 20 sm.
  • the core layer of the film had a thickness of 16 ⁇ m, and the outer layers arranged on both sides of the core layer each had a thickness of 2 ⁇ m.
  • the in-plane retardation of the obtained cellulose acylate film 1 was 0 nm.
  • the coating liquid for forming a photo-alignment film P-4 having the following composition was continuously applied onto the cellulose acylate film 1 with a wire bar of #2.4.
  • the cellulose acylate film 1 on which the coating film had been formed was dried with hot air at 140° C. for 120 seconds, and subsequently irradiated with polarized ultraviolet rays at 10 mJ/cm 2 (measurement wavelength of 315 nm using a ultra-high pressure mercury lamp) through a wire grid polarizer (ProFlux PPL02, manufactured by Moxtek, Inc.) to form a photo-alignment film P-4.
  • polarized ultraviolet rays 10 mJ/cm 2 (measurement wavelength of 315 nm using a ultra-high pressure mercury lamp)
  • wire grid polarizer ProFlux PPL02, manufactured by Moxtek, Inc.
  • composition A-1 was applied onto the photo-alignment film P-4 using a bar coater.
  • the coating film formed on the photo-alignment film P-4 was heated to 145° C. with hot air and then cooled to 70° C., and the coating film was irradiated with ultraviolet rays at 100 mJ/cm 2 at a wavelength of 365 nm in a nitrogen atmosphere using a high-pressure mercury lamp and subsequently irradiated with ultraviolet rays at 500 mJ/cm 2 under heating to 120° C. to fix the alignment of the liquid crystal compound, thereby manufacturing an optical film including an optically anisotropic layer (positive A-plate).
  • the thickness of the optically anisotropic layer is shown in Table 3 below.
  • a film C-1 having a positive C-plate C-1 on a temporary support for formation was manufactured by the same method as for the positive C-plate described in paragraph [0124] of JP2015-200861A. It should be noted that the thickness of the positive C-plate was controlled so that Rth(550) was ⁇ 69 nm.
  • a surface of a TD80UL (manufactured by FUJIFILM Corporation) which is a support was subjected to an alkali saponification treatment. Specifically, the support was immersed in a 1.5 N aqueous sodium hydroxide solution at 55° C. for 2 minutes, and the extracted support was washed in a water-washing bathtub at room temperature and neutralized with 0.1 N sulfuric acid at 30° C. Thereafter, the obtained support was washed in a water-washing bathtub at room temperature and further dried with a hot air at 100° C.
  • a roll-shaped polyvinyl alcohol film having a thickness of 80 ⁇ m was continuously stretched five times in an iodine aqueous solution, and the stretched film was dried to obtain a polarizer having a thickness of 20 ⁇ m.
  • the obtained polarizer was bonded to a support (TD80UL) which had been subjected to an alkali saponification treatment were bonded to each other to obtain a polarizing plate 0 in which the polarizer was exposed on one side.
  • the polarizer of the polarizing plate 0 and the coating surface of the positive A-plate were bonded to each other using a pressure sensitive adhesive (SK-2057, manufactured by Soken Chemical Co., Ltd.) so that the absorption axis of the polarizer and the slow axis of the optically anisotropic layer (positive A-plate) manufactured in Examples 31 to 33 were orthogonal to each other.
  • a pressure sensitive adhesive (SK-2057, manufactured by Soken Chemical Co., Ltd.) so that the absorption axis of the polarizer and the slow axis of the optically anisotropic layer (positive A-plate) manufactured in Examples 31 to 33 were orthogonal to each other.
  • the coating surface of the positive C-plate C-1 in the film C-1 was bonded onto a surface of the transferred positive A-plate using a pressure sensitive adhesive (SK-2057, manufactured by Soken Chemical Co., Ltd.), and the support of the film C-1 was peeled to transfer only the positive C-plate C-1 onto the positive A-plate A, thereby manufacturing polarizing plates 1 to 3.
  • a pressure sensitive adhesive (SK-2057, manufactured by Soken Chemical Co., Ltd.)
  • a polarizing plate on the visible side was peeled from a liquid crystal cell of iPad (registered trademark, manufactured by Apple) and used as an IPS-mode liquid crystal cell.
  • Each of the polarizing plates 1 to 3 manufactured above instead of the peeled polarizing plate was as bonded onto the liquid crystal cell to manufacture a liquid crystal display device.
  • the bonding was performed such that the absorption axis of the polarizing plate and the optical axis of the liquid crystal layer in the liquid crystal cell were perpendicular to each other as observed from a direction vertical to the substrate surface of the liquid crystal cell at the time of a voltage being off.
  • the light incidence angle dependence of Re was measured at wavelengths of 450 nm and 550 nm, using AxoScan OPMF-1 (manufactured by Opto Science, Inc.). The results are shown in Table 5 below.
  • a polarizing plate 0 in which the positive A-plate and the positive C-plate had not been bonded to each other was directly bonded to a liquid crystal display device.
  • a luminance (Yw) in the direction vertical to a panel in a white display and a luminance (Yb) in the direction vertical to a panel in a black display were measured using a commercially available measuring apparatus for a liquid crystal viewing angle and chromaticity characteristics, Ezcontrast (manufactured by ELDIM), and a contrast ratio (Yw/Yb) in the direction vertical to the panel was calculated and taken as a front contrast, and evaluated according to the following standard. The results are shown in Table 3 below.
  • the front contrast is 95% or more with respect to the polarizing plate 0.
  • the front contrast is 85% or more and less than 95% with respect to polarizing plate 0.
  • the front contrast is 75% or more and less than 85% with respect to polarizing plate 0.
  • the front contrast is less than 75% with respect to polarizing plate 0.
  • a tint change is not visually recognized for a sample which has not been exposed to a high temperature.
  • a tint change is significant and not acceptable for a sample which has not been exposed to a high temperature.

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